An Enterprise, such as, a business organization, can store data that may have sensitive content. Such sensitive data can come in the form of private or company information, intellectual property (IP), financial or patient information, credit-card data, and other information depending on the business and the industry. Data loss prevention (DLP) solutions generally detect sensitive data in documents and prevent unauthorized access, saving and/or sharing of the sensitive data. Traditional DLP solutions typically prevent unauthorized access, saving and/or sharing of the sensitive data by monitoring, detecting and blocking sensitive data while in-use (endpoint actions), in-motion (network traffic), and at-rest (data storage). Users may attempt to copy the sensitive data to an unauthorized location, such as removable media. The sensitive data may be stored in digital files. For example, a user may attempt to copy a file containing confidential employee information from a work system to a removable Universal Serial Bus (“USB”) storage device (e.g., USB flash drive). Protection from copying sensitive data to unauthorized media is extremely important, as the copies of the sensitive data may subsequently be easily distributed. Existing DLP solutions are inefficient, difficult to implement, and/or have security holes in which the sensitive data may be lost. For example, existing solutions typically allow a file to be first copied from a local storage to the removable media (e.g., USB flash drive) before the file is scanned for sensitive data. Once the file copy operation is complete, the copied file on the removable media is scanned for sensitive data. The copied file is subsequently deleted if the copied file contains sensitive data. Conventional solutions generally have security flaws in that a user may eject the removable media after the file has been copied, but before the scan for sensitive data occurs, thereby bypassing the deleting of the sensitive file from the removable media. Additionally, conventional solutions are generally inefficient because the scan for sensitive data is performed on the removable media after the file is copied to the removable media, and in some cases, the scanning of the removable media can be 3-4 times slower than scanning the local storage. Other traditional solutions involve modifying specific applications to perform a scan for sensitive data prior to the file copy. However, such traditional solutions are application specific, which generally require modification of the various available applications to ensure security. Such traditional solutions are complex and can be difficult to maintain. Additionally, such conventional solutions are not very stable and may cause an application to fail.